Insights into the missing apiosylation step in flavonoid apiosides biosynthesis of Leguminosae plants

Hao-Tian Wang, Zi-Long Wang, Kuan Chen, Ming-Ju Yao, Meng Zhang, Rong-Shen Wang, Jia-He Zhang, Hans Ågren, Fu-Dong Li, Junhao Li (), Xue Qiao () and Min Ye ()
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Hao-Tian Wang: Peking University
Zi-Long Wang: Peking University
Kuan Chen: Peking University
Ming-Ju Yao: Peking University
Meng Zhang: Peking University
Rong-Shen Wang: Peking University
Jia-He Zhang: Peking University
Hans Ågren: Uppsala University
Fu-Dong Li: University of Science and Technology of China
Junhao Li: Uppsala University
Xue Qiao: Peking University
Min Ye: Peking University

Nature Communications, 2023, vol. 14, issue 1, 1-16

Abstract: Abstract Apiose is a natural pentose containing an unusual branched-chain structure. Apiosides are bioactive natural products widely present in the plant kingdom. However, little is known on the key apiosylation reaction in the biosynthetic pathways of apiosides. In this work, we discover an apiosyltransferase GuApiGT from Glycyrrhiza uralensis. GuApiGT could efficiently catalyze 2″-O-apiosylation of flavonoid glycosides, and exhibits strict selectivity towards UDP-apiose. We further solve the crystal structure of GuApiGT, determine a key sugar-binding motif (RLGSDH) through structural analysis and theoretical calculations, and obtain mutants with altered sugar selectivity through protein engineering. Moreover, we discover 121 candidate apiosyltransferase genes from Leguminosae plants, and identify the functions of 4 enzymes. Finally, we introduce GuApiGT and its upstream genes into Nicotiana benthamiana, and complete de novo biosynthesis of a series of flavonoid apiosides. This work reports an efficient phenolic apiosyltransferase, and reveals mechanisms for its sugar donor selectivity.

Date: 2023
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DOI: 10.1038/s41467-023-42393-1

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